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Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles

Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.

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Benzothiophene – Wikipedia,
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Photochromic compounds, the photochromic material, and light control member (by machine translation)

[A] is colored by UV irradiation rapidly, colored heat fading rate control compound. (1) Of a formula [solution], a diarylethene compound. In the formula, A1 – A4 The, H, halogen, alkyl or the like; X1 X and2 The, S, O, NR (R is H or alkyl) or SO2 , ; Y1 And Y2 The, or N C; R1 And R2 The, H, halogen, alkyl or the like; R3 And R4 The, Y1 Or Y2 C cases where, H, halogen, alkyl or the like, or R5 Or R6 Coupled to the ring structure, Y1 Or Y2 N the case, electron pair; R5 And R6 The, H, halogen, alkyl or the like, or R3 Or R4 Bound form a ring structure. [Drawing] no (by machine translation)

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The considerable photostability improvement of photochromic terarylene by sulfone group

Photochromic terarylene derivative 4 which has a sulfone group at the upper benzothiophene ring is readily synthesized using Suzuki coupling reaction. It exhibits good photochromic properties. Interestingly, the closed form of the compound 4 shows a good photostability as well as a thermal stability compared with its reduced analog 3, that provides a method to enhance the photostability of versatile photochromic terarylenes under UV.

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Substituent and solvent effects on the fluorescent and photochromic properties of 2-(2-pyridyl)imidazole containing diarylethene derivatives

Five diarylethene derivatives with 2-(2-pyridyl)imidazole as the ethene bridges (PI-BTEs) were synthesized and characterized. The structures and performances of the PI-BTEs (L1-L5) could be modified from not only the thiophene unit, but also the substituent on the imidazole nitrogen. Noteworthily, replacing the thiophene with the benzothiophene, the fatigue resistance is significantly improved, the centre absorption bands of the closed forms shift from 572 nm (L3) to 550 nm (L2), and the colours of the solutions change from pale pink in L3 to red-purple in L2. Additionally, the Stokes shift (Deltanu) values of L3 in various solvents display good linear relationships with the donor number (DN) of the solvents, and the solvent polarity parameter Deltaf.

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Photochromic dihetarylethenes. 12.* Synthesis of 5-alkyl-2- (1,3,4-oxadiazol-2-yl)thiophenes and their photochromic derivatives

Photochromic derivatives of 5-alkyl-2-(1,3,4-oxadiazol-2-yl)thiophenes have been synthesized for the first time. Their photochromic and fluorescent properties have been studied.

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Benzothiophene – Wikipedia,
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Rational design of a visible-light photochromic diarylethene: a simple strategy by extending conjugation with electron donating groups

Photochromic diarylethenes have been widely used in many fields. However, their cyclization process must be induced by UV light. In this article, a simple strategy is developed by extending pi-conjugation with electron donating groups. The modified dirylethene derivative can photocyclolize under 405-nm light with a good photochromic efficiency. Meanwhile, its absorption and moderate fluorescence can be switched effectively in both directions by visible lights (405 and 520 nm, respectively) in different solutions and in living cells. We believe that this simple method will become a versatile strategy for developing various dirylethylenes with visible-light photochromism.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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With the Hg2 + And Cys continuous selective asymmetric perfluoro cyclopentene compound and its preparation method and application (by machine translation)

The invention discloses a [1 – [2 – methyl – 3 – benzothienyl], 2 – (2 – methyl – 5 – (4 – phenyl) – (2 – formyl quinoline – 8 – benzothiazolyl) – 3 – thienyl)] full-PVC pentene and its preparation method and application. Preparation method: to benzo thiophene as raw materials, through the iodomethane substituted, brominated, with the perfluoro pentene reaction to generate single substituted perfluoro pentene; to 2 – methyl thiophene as raw materials, bromination, through the n-BuLi and tributyl borate reaction, Stuzki coupling reaction through the end of the with the thiophene ring containing aldehyde group benzene connected, then with ethylene glycol protection after single substituted perfluoro pentene reaction, by reducing dioxiding hydroxy, any change of containing methyl radical bromine, with 8 – hydroxy quinoline – 2 – aldehyde reaction, finally with 2 – amino thiophenol reaction, to obtain the target compound. Prepared by the invention compounds can be used for continuous detection of a specific ion and amino acid, its selectivity is very good. (by machine translation)

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Reversibly photoswitchable nucleosides: Synthesis and photochromic properties of diarylethene-functionalized 7-deazaadenosine derivatives

Photochromic nucleosides were designed that combine the structural features and molecular recognition properties of nucleic acids with the light-sensitivity of diarylethenes. Target compounds 1a-c consist of a 7-deazaadenosine unit that is linked to a thiophene as the second aryl functionality via a 1,2-cyclopentenyl linker. These nucleoside analogues undergo a reversible electrocyclic rearrangement, generating strongly colored closed-ring isomers upon irradiation with UV-light, while exposure to light in the visible range triggers the cycloreversion to the colorless opened-ring form. UV-vis spectroscopy, HPLC, and 1H NMR measurements revealed recognition of complementary thymidine and up to 97% conversion to the thermally stable closed-ring isomers after illumination with UV-light. The required wavelength for ring closure was found to vary depending on the substituents attached to the thiophene moiety. In a first design step, we used this important feature of diarylethenes to shift the switching wavelength from initially 300 nm (1a) to 405 nm (1cH+). In a second step, we generated a pair of orthogonal switches, differing enough in their respective switching wavelengths to be controlled independently in the same sample. Finally, a molecular switch was developed that showed both photochromism and acidichromism, thereby illustrating the possibility to gate the spectral properties to multiple stimuli. These new photochromic nucleosides represent useful building blocks for the generation of light-sensitive nucleic acids either by inducing conformational changes upon isomerization or by exploring the different spectral properties of the closed and opened isomers, for example, for use as reversible fluorescence quenchers.

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Benzothiophene – Wikipedia,
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The effects of heteroaryl ring on the photochromism of diarylethenes with a naphthalene moiety

Three new asymmetrical naphthalene-containing diarylethenes with different heteroaryl groups have been synthesized to investigate the heteroaryl effects on their properties. The three diarylethenes exhibited distinctive photochromism with good thermal stability, which may be attributed to the different heteroaryl effects. Their cycloreversion quantum yields increased in the order of 2-methylbenzofuran < 2-methylbenzothiophene < 1,2-dimethylindole, while the cyclization quantum yields exhibited a reverse trend. Compared to indole and benzothiophene, the benzofuran moiety could effectively shift the absorption maximum to a shorter wavelength and notably enhance the cyclization quantum yield and fluorescence quantum yield of the diarylethene. The results indicated that the category of heteroaryl groups played a vital role during the process of photoisomerization of naphthalene-containing diarylethene derivatives. If you are interested in 10243-15-9, you can contact me at any time and look forward to more communication. Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene

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Dihydropyridines useful in the treatment of angina and stroke

This invention provides certain substituted dihydropyridines, their pharmaceutical formulations, and their use for causing vasodilation in mammals.

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